Epoxy compound, curable composition containing the same, and cured product obtained by curing curable composition

ABSTRACT

The present invention discloses a composition comprising at least one or more stereoisomers of a compound represented by the following Formula (1), wherein, in a gas chromatogram obtained by analyzing the composition by gas chromatography, the ratio of the area of the maximum peak with respect to the total area of peaks derived from the stereoisomers is 60% or more; and wherein the maximum peak is present within the range of retention time of from 27.6 to 28.0 minutes. The present invention also discloses: a curable composition comprising the above described composition, and one selected from the group consisting of a thermal cationic polymerization initiator, an acid anhydride-based curing agent and a curing accelerator, and a photo-cationic polymerization initiator; as well as a cured product therefrom. The above described curable composition is useful in that it allows for the production of a cured product having a high heat resistance. 
                         
(In the Formula (1), R 1  to R 18  are each independently selected from the group consisting of a hydrogen atom, an alkyl group and an alkoxy group.)

CROSS-REFERENCE TO RELATED APPLICATIONS

The present patent application is based upon and claims the benefit ofpriority from previously filed Japanese Patent Application No.2016-116591 (filed on Jun. 10, 2016), and Japanese Patent ApplicationNo. 2016-206395 (filed on Oct. 20, 2016). The entire disclosures of theabove described patent applications are incorporated herein byreference.

BACKGROUND OF THE INVENTION Field of the Invention

The present invention relates to an epoxy compound, a curablecomposition containing the same, and a cured product obtained fromcuring the curable composition.

Background Art

Curable compositions containing epoxy compounds are used as materialsfor surface protective films for semiconductor devices and organic thinfilm elements (such as organic electro-luminescent elements and organicthin film solar cell elements), interlayer insulators, protectiveinsulating films for printed alignment substrates, and fiber-reinforcedcomposite materials and the like. Among these epoxy compounds, epoxycompounds containing an aromatic ring have been used as compounds whichallow for the production of cured products having an excellent heatresistance and the like.

However, compounds containing an aromatic ring generally have a highdielectric constant due to having a high electron density, andaccordingly, in the applications as described above, there has been aproblem for use in the field of electronic materials. Further, thesecompounds are also associated with a problem that coloration and thelike thereof lead to a reduction in the light transmittance of theresulting resin. In view of the above, alicyclic diamine compoundshaving no aromatic ring are drawing attention, in recent years. Inaddition, curable compositions for use in the applications as describedabove are required to be able to produce cured products having a highmoisture resistance and heat resistance.

Among epoxy compounds, epoxy compounds having an alicyclic skeleton areknown as compounds which allow for the production of cured productshaving an excellent heat resistance and the like. For example, PatentDocument 1 discloses an epoxy compound which has an alicyclic skeletonwith a specific structure and which allows for the production of a resinhaving an excellent heat resistance and the like.

Further, among these epoxy compounds, epoxy compounds having two or morealicyclic skeletons within the molecule are known as compounds whichallow for the production of cured products having an excellent heatresistance, transparency and the like. For example, Patent Document 2discloses a curable composition containing dicyclopentadiene diepoxideor tricyclopentadiene diepoxide. In addition, Patent Document 3discloses a curable composition containing a diepoxybicyclohexylcompound. However, the epoxy compounds having alicyclic skeletons whichare proposed in Patent Documents 2 and 3 have room for a furtherimprovement, from the viewpoint of improving the heat resistance of theresulting cured products and avoiding decreasing the weight reductionupon curing.

PRIOR ART DOCUMENTS Patent Documents

Patent Document 1: JP S49-126658 A

Patent Document 2: JP 2004-143362 A

Patent Document 3: JP 2008-31424 A

SUMMARY OF THE INVENTION Problems to be Solved by the Invention

The present inventors have found out that the heat resistance of curedproducts obtained by curing the curable compositions disclosed in PatentDocuments 2 and 3, and the like are not yet sufficient, and there isroom for a further improvement.

Further, the present inventors have found out that, in a composition ofan epoxy compound comprising one or more stereoisomers having a specificstructure, it is possible to dramatically improve the heat resistance ofa cured product obtained by curing a curable composition containing theabove described composition, by adjusting the ratio of a peak area(s)derived from a stereoisomer(s) having a specific retention time withrespect to the total area of peaks derived from the stereoisomerscontained in the composition to equal to or more than a specificnumerical value. In addition, the present inventors have clarified thespecific steric structure of the stereoisomer corresponding to themaximum peak.

The present invention has been made based on the above findings, and anobject of the invention is to provide a composition, or an epoxycompound having a specific stereoisomeric structure, which allows forproducing a cured product having a markedly improved heat resistance.

Means for Solving the Problems

In other words, the present invention encompasses the followinginventions.

[1] A composition comprising at least one or more stereoisomers of acompound represented by the following Formula (1):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group)

wherein, in a gas chromatogram obtained by analyzing the composition bygas chromatography under the following analysis conditions, the ratio ofthe area of the maximum peak with respect to the total area of peaksderived from the stereoisomers is 60% or more,

wherein the maximum peak is present within the range of retention timeof from 27.6 to 28.0 minutes, and

wherein the analysis conditions are as follows:

column: HP-1 (manufactured by Agilent Technologies Inc.),

length: 60.0 m, inner diameter: 250 μm, film thickness: 0.25 μm;

liquid phase: 100% dimethylpolysiloxane;

carrier gas: N₂;

flow velocity: 1.3 mL/min;

sample inlet temperature: 140° C.;

detector temperature: 250° C.;

sample injection volume: 0.2 μL; and

temperature increase conditions: 80° C. (3 min), 80 to 150° C. (10°C./min), 150 to 250° C. (5° C./min), 250° C. (20 min).

[2] A composition comprising at least one or more stereoisomers of acompound represented by the following Formula (1):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group)

wherein, in a gas chromatogram obtained by analyzing the composition bygas chromatography under the following analysis conditions, the ratio ofthe area of the maximum peak within the range of retention time of from27.6 to 28.0 minutes with respect to the total area of peaks within therange of retention time of from 27.5 to 29.0 minutes is 60% or more, and

wherein the analysis conditions are as follows:

column: HP-1 (manufactured by Agilent Technologies Inc.),

length: 60.0 m, inner diameter: 250 μm, film thickness: 0.25 μm;

liquid phase: 100% dimethylpolysiloxane;

carrier gas: N₂;

flow velocity: 1.3 mL/min;

sample inlet temperature: 140° C.;

detector temperature: 250° C.;

sample injection volume: 0.2 μL; and

temperature increase conditions: 80° C. (3 min), 80 to 150° C. (10°C./min), 150 to 250° C. (5° C./min), 250° C. (20 min).

[3] The composition according to [1] or [2], wherein the compoundrepresented by the Formula (1) is a reaction product of a compoundrepresented by the following Formula (2):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group)with a peracid.[4] The composition according to any one of [1] to [3], wherein themaximum peak is the first peak among the peaks derived from thestereoisomers.[5] The composition according to any one of [1] to [3], wherein themaximum peak is the first peak appearing after a retention time of 27.5minutes, among the peaks within the range of retention time of from 27.5to 29.0 minutes.[6] The composition according to any one of [1] to [5], wherein the R¹to R¹⁸ are all hydrogen atoms.[7] The composition according to any one of [1] to [6], wherein thestereoisomer corresponding to the maximum peak is represented by thefollowing Formula (3):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group).[8] An epoxy compound represented by the following Formula (3):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group).[9] A curable composition comprising:

the composition according to any one of [1] to [7] or the epoxy compoundaccording to [8]; and

one selected from the group consisting of: a thermal cationicpolymerization initiator, an acid anhydride-based curing agent and acuring accelerator, and a photo-cationic polymerization initiator.

[10] The curable composition according to [9], further comprising onekind, or two or more kinds selected from the group consisting of anepoxy compound other than the compound represented by the Formula (1),an oxetane compound and a vinyl ether.

[11] The curable composition according to [9] or [10], wherein thethermal cationic polymerization initiator is selected from the groupconsisting of aromatic sulfonium salt-based thermal cationicpolymerization initiators, aromatic iodonium salt-based thermal cationicpolymerization initiators and aluminum complex-based thermal cationicpolymerization initiators.[12] The curable composition according to [11], wherein the thermalcationic polymerization initiator is an aromatic sulfonium salt-basedthermal cationic polymerization initiator.[13] The curable composition according to any one of [10] to [12],wherein, in cases where the curable composition does not include any ofthe epoxy compound other than the compound represented by the Formula(1), the oxetane compound and the vinyl ether, the content of thethermal cationic polymerization initiator is from 0.1 to 15 parts bymass with respect to 100 parts by mass of the composition according toany one of [1] to [7] or the epoxy compound according to [8] containedin the curable composition; and in cases where the curable compositionincludes one kind, or two or more kinds selected from the groupconsisting of the epoxy compound other than the compound represented bythe Formula (1), the oxetane compound and the vinyl ether, the contentof the thermal cationic polymerization initiator is from 0.1 to 15 partsby mass with respect to 100 parts by mass of the total amount of thecomposition according to any one of [1] to [7] or the epoxy compoundaccording to [8], the epoxy compound other than the compound representedby the Formula (1), the oxetane compound and the vinyl ether, which arecontained in the curable composition.[14] The curable composition according to [10], wherein, in cases wherethe curable composition does not include the epoxy compound other thanthe compound represented by the Formula (1), the content of the acidanhydride-based curing agent is from 0.6 to 1.2 equivalents with respectto one epoxy equivalent of the composition according to any one of [1]to [7] or the epoxy compound according to [8] contained in the curablecomposition; and in cases where the curable composition includes theepoxy compound other than the compound represented by the Formula (1),the content of the acid anhydride-based curing agent is from 0.6 to 1.2equivalents with respect to one epoxy equivalent of a mixture of epoxycompounds composed of the composition according to any one of [1] to [7]or the epoxy compound according to [8] and the epoxy compound other thanthe compound represented by the Formula (1), which are contained in thecurable composition.[15] The curable composition according to [10] or [14], wherein, incases where the curable composition does not include the epoxy compoundother than the compound represented by the Formula (1), the content ofthe curing accelerator is from 0.1 to 10 parts by mass with respect to100 parts by mass of the composition according to any one of [1] to [7]or the epoxy compound according to [8] contained in the curablecomposition; and in cases where the curable composition includes theepoxy compound other than the compound represented by the Formula (1),the content of the curing accelerator is from 0.1 to 10 parts by masswith respect to 100 parts by mass of the total amount of the compositionaccording to any one of [1] to [7] or the epoxy compound according to[8] and the epoxy compound other than the compound represented by theFormula (1), which are contained in the curable composition.[16] The curable composition according to [9], [14] or [15], wherein thecuring accelerator is an imidazole-based curing accelerator.[17] The curable composition according to any one of [11] to [16],wherein the content of the composition according to any one of [1] to[7] or the epoxy compound according to [8] is from 10 to 99% by mass.[18] The curable composition according to [9] or [10], wherein thephoto-cationic polymerization initiator is an aromatic sulfoniumsalt-based photo-cationic polymerization initiator.[19] The curable composition according to [10] or [18], wherein, incases where the curable composition does not include any of the epoxycompound other than the compound represented by the Formula (1), theoxetane compound and the vinyl ether, the content of the photo-cationicpolymerization initiator is from 0.1 to 20 parts by mass with respect to100 parts by mass of the composition according to any one of [1] to [7]or the epoxy compound according to [8] contained in the curablecomposition; and in cases where the curable composition includes onekind, or two or more kinds selected from the group consisting of theepoxy compound other than the compound represented by the Formula (1),the oxetane compound and the vinyl ether, the content of thephoto-cationic polymerization initiator is from 0.1 to 20 parts by masswith respect to 100 parts by mass of the total amount of the compositionaccording to any one of [1] to [7] or the epoxy compound according to[8], the epoxy compound other than the compound represented by theFormula (1), the oxetane compound and the vinyl ether, which arecontained in the curable composition.[20] The curable composition according to [18] or [19], wherein thecontent of the composition according to any one of [1] to [7] or theepoxy compound according to [8] is from 1 to 50% by mass.[21] The curable composition according to any one of [10] to [20],wherein the epoxy compound other than the compound represented by theFormula (1) is selected from the group consisting of glycidyl ether-typeepoxides, glycidyl ester-type epoxides and alicyclic epoxides.[22] A method of producing a cured product, the method comprising thestep of curing the curable composition according to any one of [9] to[21].[23] A cured product from the curable composition according to any oneof [9] to [21].

Effect of the Invention

The present invention provides a composition or an epoxy compound whichallows for the production of a cured product having a high heatresistance.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows a gas chromatograph of a composition (A-1) prepared inPreparation Example 1.

FIG. 2 shows a gas chromatograph of a composition (A-2) prepared inPreparation Example 2.

FIG. 3 shows a gas chromatograph of a composition (A-3) prepared inPreparation Example 3.

FIG. 4 shows a gas chromatograph of a composition (A-4) prepared inPreparation Example 4.

FIG. 5 shows a gas chromatograph of a composition (A-5) prepared inPreparation Example 5.

FIG. 6 is a chart showing ¹H NMR peaks of the composition (A-5) preparedin Preparation Example 5.

FIG. 7 is a chart showing ¹³C NMR peaks of the composition (A-5)prepared in Preparation Example 5.

DETAILED DESCRIPTION OF THE INVENTION 1. Definitions

In the present specification, the terms “part(s)”, “%” and the like usedto describe the composition are represented on a mass basis, unlessotherwise specified.

In the present specification, the term “epoxy equivalent” is defined bythe mass of an epoxy compound containing one equivalent of epoxy groups.In the case of a mixture composed of m kinds (wherein m is an integer of2 or more) of epoxy compounds, the epoxy equivalent of the mixture isrepresented by the following equation:

$\begin{matrix}{\lbrack {{Math}\mspace{14mu} 1} \rbrack\mspace{670mu}{{{Epoxy}\mspace{14mu}{equivalent}\mspace{14mu}{of}\mspace{14mu} a\mspace{14mu}{mixture}\mspace{14mu}{of}\mspace{14mu}{epoxy}\mspace{14mu}{compounds}} = \frac{\sum\limits_{n = 1}^{n}\;{{Mass}\mspace{14mu}{of}\mspace{14mu}{epoxy}\mspace{14mu}{compound}\mspace{14mu} n}}{\sum\limits_{n = 1}^{n}\;\frac{{Mass}\mspace{14mu}{of}\mspace{14mu}{epoxy}\mspace{14mu}{compound}\mspace{14mu} n}{{Epoxy}\mspace{14mu}{equivalent}\mspace{14mu}{of}\mspace{14mu}{epoxy}\mspace{14mu}{compound}\mspace{14mu} n}}}} & \;\end{matrix}$

The epoxy equivalent of an epoxy compound can be measured in accordancewith JIS K7236.

2. Composition Comprising Stereoisomers of Epoxy Compound

The composition according to the present invention is a compositioncomprising at least one or more stereoisomers of a compound representedby the following Formula (1), wherein, in a gas chromatogram obtained byanalyzing the composition by gas chromatography under the followinganalysis conditions, the ratio of the area of the maximum peak withrespect to the total area of peaks derived from the stereoisomers is 60%or more, and wherein the maximum peak is present within the range ofretention time of from 27.6 to 28.0 minutes. Further, the compositionaccording to the present invention is a composition comprising at leastone or more stereoisomers of a compound represented by the followingFormula (1), wherein, in a gas chromatogram obtained by analyzing thecomposition by gas chromatography under the following analysisconditions, the ratio of the area of the maximum peak within the rangeof retention time of from 27.6 to 28.0 minutes with respect to the totalarea of peaks within the range of retention time of from 27.5 to 29.0minutes is 60% or more.

(In the Formula (1), R¹ to R¹⁸ are each independently selected from thegroup consisting of a hydrogen atom, an alkyl group and an alkoxygroup.)(Analysis Conditions)Column: HP-1 (manufactured by Agilent Technologies Inc.),length: 60.0 m, inner diameter: 250 μm, film thickness: 0.25 μmLiquid phase: 100% dimethylpolysiloxaneCarrier gas: N₂Flow velocity: 1.3 mL/minSample inlet temperature: 140° C.Detector temperature: 250° C.Sample injection volume: 0.2 μLTemperature increase conditions: 80° C. (3 min), 80 to 150° C. (10°C./min), 150 to 250° C. (5° C./min), 250° C. (20 min

The composition according to the present invention comprises at leastone or more stereoisomers of a compound represented by the Formula (1).

The epoxy compound according to the present invention is characterizedin that it is represented by the following Formula (3):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group).

In the composition according to the present invention or the epoxycompound according to the present invention, R¹ to R¹⁸ in the abovedescribed Formula (1) or the above described Formula (3) are eachindependently selected from the group consisting of a hydrogen atom, analkyl group and an alkoxy group. Among these, R¹ to R¹⁸ are particularlypreferably hydrogen atoms. The alkyl group preferably has from 1 to 10carbon atoms, and more preferably from 1 to 5 carbon atoms. Further, thealkyl group may be a linear alkyl group or a branched alkyl group. Thealkoxy group preferably has from 1 to 10 carbon atoms, and morepreferably from 1 to 5 carbon atoms. It is particularly preferred thatR¹ to R¹⁸ be all hydrogen atoms.

In the case of a curable composition containing the compositionaccording to the present invention or the epoxy compound according tothe present invention and a thermal cationic polymerization initiator,or alternatively, in the case of a curable composition containing thecomposition according to the present invention or the epoxy compoundaccording to the present invention, an acid anhydride-based curing agentand a curing accelerator, the composition according to the presentinvention or the epoxy compound according to the present inventioncontained in the curable composition preferably has an epoxy equivalentof from 85 to 600 g/eq, more preferably from 90 to 600 g/eq, still morepreferably from 85 to 300 g/eq, still more preferably from 90 to 300g/eq, and yet still more preferably from 90 to 200 g/eq. The curablecomposition according to the present invention may further contain anyof other compounds to be described later. However, the content of thecomposition according to the present invention or the epoxy compoundaccording to the present invention contained in the curable compositionaccording to the present invention is preferably from 10 to 99% by mass,more preferably from 10 to 80% by mass, still more preferably from 15 to99% by mass, and yet still more preferably from 15 to 60% by mass, fromthe viewpoint of improving heat resistance of the resulting curedproduct and/or preventing a reduction in weight upon curing.

In the case of a curable composition containing the compositionaccording to the present invention or the epoxy compound according tothe present invention and a photo-cationic polymerization initiator, thecomposition according to the present invention or the epoxy compoundaccording to the present invention contained in the curable compositionpreferably has an epoxy equivalent of from 85 to 600 g/eq, morepreferably from 85 to 300 g/eq, and still more preferably from 85 to 200g/eq. The curable composition according to the present invention mayfurther contain any of other compounds to be described later. However,the content of the composition according to the present invention or theepoxy compound according to the present invention contained in thecurable composition according to the present invention is preferablyfrom 1 to 50% by mass, and more preferably from 5 to 40% by mass, fromthe viewpoint of improving the heat resistance the resulting curedproduct.

In the gas chromatogram obtained by analyzing the composition accordingto the present invention by gas chromatography under the above describedanalysis conditions, the ratio of the area of the maximum peak withrespect to the total area of peaks derived from the stereoisomers of thecompound represented by the above described Formula (1) which arecontained in the composition is 60% or more. The ratio is preferably 62%or more, 70% or more, 80% or more, 84% or more, 91% or more, or 96% ormore. Further, the maximum peak is present within the range of retentiontime of from 27.6 to 28.0 minutes.

In the gas chromatogram obtained by analyzing the composition accordingto the present invention by gas chromatography under the above describedanalysis conditions, the ratio of the area of the maximum peak withinthe range of retention time of from 27.6 to 28.0 minutes with respect tothe total area of peaks within the range of retention time of from 27.5to 29.0 minutes is 60% or more. The ratio is preferably 62% or more, 70%or more, 80% or more, 84% or more, 91% or more, or 96% or more.

In the composition according to the present invention, the stereoisomercorresponding to the maximum peak is preferably represented by thefollowing Formula (3):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group).

R¹ to R¹⁸ in the Formula (3) are the same as defined in the abovedescribed Formula (1).

As shown in the following conditions, the column to be used in achromatography analysis is composed of dimethylsiloxane. For example, itis possible to use Agilent 19091Z-436E, manufactured by AgilentTechnologies Inc., or the like

(Analysis Conditions)

Measurement apparatus: Agilent 6850 series, manufactured by AgilentTechnologies Inc.

Column: HP-1 (manufactured by Agilent Technologies Inc.),

length: 60.0 m, inner diameter: 250 μm, film thickness: 0.25 μm

Liquid phase: 100% dimethylpolysiloxane

Carrier gas: N₂

Flow velocity: 1.3 mL/min

Sample inlet temperature: 140° C.

Detector temperature: 250° C.

Sample injection volume: 0.2 μL

Temperature increase conditions: 80° C. (3 min), 80 to 150° C. (10°C./min), 150 to 250° C. (5° C./min), 250° C. (20 min)

The maximum peak in the composition according to the present inventionpreferably appears first of all the peaks derived from the stereoisomerscontained in the composition. More specifically, the maximum peak ispreferably a peak which appears first within the retention time of from27.5 to 30.0 minutes.

Further, the maximum peak in the composition according to the presentinvention is preferably the first peak appearing after a retention timeof 27.5 minutes, among the peaks within the range of retention time offrom 27.5 to 29.0 minutes.

In the composition according to the present invention, it is preferredthat R¹ to R¹⁸ in the above described Formula (1) be all hydrogen atoms.

In the present invention, the compound represented by the Formula (1) ispreferably a reaction product of a compound represented by the followingFormula (2):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group)with a peracid.

R¹ to R¹⁸ in the Formula (2) are the same as defined in the abovedescribed Formula (1).

In one embodiment, the compound represented by the Formula (1) can besynthesized by allowing the compound represented by the Formula (2) toreact with a peracid, such as hydrogen peroxide, peracetic acid orperbenzoic acid.

In one embodiment, the compound satisfying the Formula (2) can besynthesized by the Diels-Alder reaction of cyclopentadiene anddicyclopentadiene.

In the composition according to the present invention, it is possible toincrease the ratio of the area of the maximum peak present within therange of retention time of from 27.6 to 28.0 minutes, by furthercarrying out purification by crystallization. More specifically, theratio of the area of the maximum peak can be increased by: dissolvingthe epoxy compound in isopropyl alcohol; cooling the resulting solutionto room temperature (25° C.) to allow crystallization to occur;filtering the resultant to obtain solids, and washing the resultingsolids with isopropyl alcohol, followed by drying.

In the composition according to the present invention, it is possible toincrease the ratio of the area of the maximum peak within the range ofretention time of from 27.6 to 28.0 minutes by further carrying outpurification by crystallization, in the gas chromatogram obtained byanalyzing the composition by gas chromatography under the abovedescribed analysis conditions. More specifically, the ratio of the areaof the maximum peak can be increased by: dissolving the epoxy compoundin isopropyl alcohol; cooling the resulting solution to room temperature(25° C.) to allow crystallization to occur; filtering the resultant toobtain solids, and washing the resulting solids with isopropyl alcohol,followed by drying.

3. Curable Composition

The curable composition according to the present invention ischaracterized in that it comprises: the composition according to thepresent invention or the epoxy compound according to the presentinvention; and one selected from the group consisting of: a thermalcationic polymerization initiator, an acid anhydride-based curing agentand a curing accelerator, and a photo-cationic polymerization initiator.

(1) Thermal Cationic Polymerization Initiator

Examples of cationic polymerization initiators which can be contained inthe curable composition according to the present invention includethermal cationic polymerization initiators (initiators capable ofgenerating cationic active species by the application of thermal energythereto) and photo-cationic polymerization initiators (initiatorscapable of generating cationic active species by the irradiation oflight or an electron beam thereto). The combined use of the compositionaccording to the present invention or the epoxy compound according tothe present invention with a thermal cationic polymerization initiatorenables to improve the heat resistance of the resulting cured product toan even higher level, as well as to decrease the reduction in the weightthereof which occurs upon curing. The above combination also enables toimprove the transparency of the resulting cured product.

The thermal cationic polymerization initiator may be, for example: (i)an aromatic sulfonium salt-based thermal cationic polymerizationinitiator; (ii) a phosphonium salt-based thermal cationic polymerizationinitiator; (iii) a quaternary ammonium salt-based thermal cationicpolymerization initiator; (iv) an aluminum complex-based thermalcationic polymerization initiator; (v) an aromatic iodonium salt-basedthermal cationic polymerization initiator; (vi) an aromatic diazoniumsalt-based thermal cationic polymerization initiator; or (vii) apyridinium-based thermal cationic polymerization initiator.

Examples of the aromatic sulfonium salt-based thermal cationicpolymerization initiator include: hexafluoroantimonate salts such as

-   (2-ethoxy-1-methyl-2-oxoethyl)methyl-2-naphthalenylsulfonium    hexafluoroantimonate,    4-(methoxycarbonyloxy)phenylbenzylmethylsulfonium    hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium    hexafluoroantimonate, 4-hydroxyphenylbenzylmethylsulfonium    hexafluoroantimonate, 4-hydroxyphenyl(o-methylbenzyl)methylsulfonium    hexafluoroantimonate,    4-hydroxyphenyl(α-naphthylmethyl)methylsulfonium    hexafluoroantimonate, diphenyl-4-(phenylthio)phenylsulfonium    hexafluoroantimonate, triphenylsulfonium hexafluoroantimonate,    bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide    bishexafluoroantimonate, and bis[4-(diphenylsulfonio)phenyl]sulfide    bishexafluoroantimonate; hexafluorophosphate salts such as    (2-ethoxy-1-methyl-2-oxoethyl)methyl-2-naphthalenylsulfonium    hexafluorophosphate, 4-acetoxyphenylbenzylmethylsulfonium    hexafluorophosphate, 4-hydroxyphenyl(o-methylbenzyl)methylsulfonium    hexafluorophosphate,    4-hydroxyphenyl(α-naphthylmethyl)methylsulfonium    hexafluorophosphate, diphenyl-4-(phenylthio)phenylsulfonium    hexafluorophosphate, triphenylsulfonium hexafluorophosphate,    bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide    bishexafluorophosphate, and bis[4-(diphenylsulfonio)phenyl]sulfide    bishexafluorophosphate; hexafluoroarsenate salts such as    4-hydroxyphenyl(o-methylbenzyl)methylsulfonium hexafluoroarsenate,    and 4-hydroxyphenylbenzylmethylsulfonium hexafluoroarsenate;    tetrafluoroborate salts such as    (2-ethoxy-1-methyl-2-oxoethyl)methyl-2-naphthalenylsulfonium    tetrafluoroborate, 4-hydroxyphenyl(o-methylbenzyl)methylsulfonium    tetrafluoroborate, 4-hydroxyphenylbenzylmethylsulfonium    tetrafluoroborate, diphenyl-4-(phenylthio)phenylsulfonium    tetrafluoroborate, triphenylsulfonium tetrafluoroborate,    bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide    bistetrafluoroborate, and bis[4-(diphenylsulfonio)phenyl]sulfide    bistetrafluoroborate; trifluoromethanesulfonate salts such as    4-hydroxyphenyl(o-methylbenzyl)methylsulfonium    trifluoromethanesulfonate, and 4-hydroxyphenylbenzylmethylsulfonium    trifluoromethanesulfonate; trifluoromethanesulfonate salts such as    diphenyl-4-(phenylthio)phenylsulfonium trifluoromethanesulfonate;    bis(trifluoromethanesulfone)imide salts such as    4-hydroxyphenyl(α-naphthylmethyl)methylsulfonium    bis(trifluoromethanesulfone)imide, and    4-hydroxyphenylbenzylmethylsulfonium    bis(trifluoromethanesulfone)imide; tetrakis(pentafluorophenyl)borate    salts such as    (2-ethoxy-1-methyl-2-oxoethyl)methyl-2-naphthalenylsulfonium    tetrakis(pentafluorophenyl)borate,    4-(methoxycarbonyloxy)phenylbenzylmethylsulfonium    tetrakis(pentafluorophenyl)borate,    4-hydroxyphenyl(o-methylbenzyl)methylsulfonium    tetrakis(pentafluorophenyl)borate,    4-hydroxyphenyl(α-naphthylmethyl)methylsulfonium    tetrakis(pentafluorophenyl)borate,    4-hydroxyphenylbenzylmethylsulfonium    tetrakis(pentafluorophenyl)borate,    diphenyl-4-(phenylthio)phenylsulfonium    tetrakis(pentafluorophenyl)borate, triphenylsulfonium    tetrakis(pentafluorophenyl)borate,    bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide    tetrakis(pentafluorophenyl)borate, and    bis[4-(diphenylsulfonio)phenyl]sulfide    tetrakis(pentafluorophenyl)borate.

Examples of (ii) the phosphonium salt-based thermal cationicpolymerization initiator include ethyltriphenylphosphoniumhexafluoroantimonate, and tetrabutylphosphonium hexafluoroantimonate.

Examples of (iii) the quaternary ammonium salt-based thermal cationicpolymerization initiator include N,N-dimethyl-N-benzylaniliniumhexafluoroantimonate, N,N-diethyl-N-benzylanilinium tetrafluoroborate,N,N-dimethyl-N-benzylpyridinium hexafluoroantimonate,N,N-diethyl-N-benzylpyridinium trifluoromethanesulfonic acid,N,N-dimethyl-N-(4-methoxybenzyl)pyridinium hexafluoroantimonate,N,N-diethyl-N-(4-methoxybenzyl)pyridinium hexafluoroantimonate,N,N-diethyl-N-(4-methoxybenzyl)toluidinium hexafluoroantimonate, andN,N-dimethyl-N-(4-methoxybenzyl)toluidinium hexafluoroantimonate.

Examples of (iv) the aluminum complex-based thermal cationicpolymerization initiator include aluminum carboxylates; aluminumalkoxide, aluminium chloride, aluminum (alkoxide) acetoacetic acidchelate, acetoacetonato aluminum, and ethylacetoacetato aluminum.

Examples of (v) the aromatic iodonium salt-based thermal cationicpolymerization initiator include phenyliodonium hexafluorophosphate,diphenyliodonium hexafluoroantimonate, diphenyliodoniumtetrafluoroborate, diphenyliodonium tetrakis(pentafluorophenyl)borate,diphenyliodonium hexafluorophosphate, diphenyliodoniumtrifluoromethanesulfonate, bis(dodecylphenyl)iodoniumhexafluorophosphate, bis(dodecylphenyl)iodonium hexafluoroantimonate,bis(dodecylphenyl)iodonium tetrafluoroborate, bis(dodecylphenyl)iodoniumtetrakis(pentafluorophenyl)borate,4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluorophosphate,4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluoroantimonate,4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrafluoroborate, and4-methylphenyl-4-(1-methylethyl)phenyliodoniumtetrakis(pentafluorophenyl)borate.

Examples of (vi) the aromatic diazonium salt-based thermal cationicpolymerization initiator include phenyldiazonium hexafluorophosphate,phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborateand phenyldiazonium tetrakis(pentafluorophenyl)borate.

Examples of (vii) the pyridinium-based thermal cationic polymerizationinitiator include 1-benzyl-2-cyanopyridinium hexafluorophosphate,1-benzyl-2-cyanopyridinium hexafluoroantimonate,1-benzyl-2-cyanopyridinium tetrafluoroborate, 1-benzyl-2-cyanopyridiniumtetrakis(pentafluorophenyl)borate, 1-(naphthylmethyl)-2-cyanopyridiniumhexafluorophosphate, 1-(naphthylmethyl)-2-cyanopyridiniumhexafluoroantimonate, 1-(naphthylmethyl)-2-cyanopyridiniumtetrafluoroborate, and 1-(naphthylmethyl)-2-cyanopyridiniumtetrakis(pentafluorophenyl)borate.

These thermal cationic polymerization initiators may be used alone, oras a mixture of two or more kinds thereof.

Among these, an aromatic sulfonium salt-based thermal cationicpolymerization initiator is more preferred, and a monoaryl-based thermalcationic polymerization initiator, such as4-acetoxyphenyldimethylsulfonium hexafluoroantimonate, is particularlypreferred. The combined use of any of these specific thermal cationicpolymerization initiators with the composition according to the presentinvention or the epoxy compound according to the present inventionenables to improve the heat resistance of the resulting cured product toan even higher level, as well as to further decrease the reduction inthe weight thereof which occurs upon curing. The above combination alsoenables to improve the transparency of the resulting cured product.

In cases where the curable composition according to the presentinvention does not contain any of an epoxy compound other than thecompound represented by the Formula (1) to be described later, anoxetane compound to be described later and a vinyl ether to be describedlater, the content of the thermal cationic polymerization initiator inthe curable composition is preferably from 0.1 to 15 parts by mass, andmore preferably from 0.3 to 7 parts by mass with respect to 100 parts bymass of the composition according to the present invention or the epoxycompound according to the present invention contained in the curablecomposition. Further, in cases where the curable composition containsone kind, or two or more kinds selected from the group consisting of theepoxy compound other than the compound represented by the Formula (1),the oxetane compound and the vinyl ether, the content of the thermalcationic polymerization initiator in the curable composition ispreferably from 0.1 to 15 parts by mass, and more preferably from 0.3 to7 parts by mass with respect to 100 parts by mass of the total amount ofthe composition according to the present invention or the epoxy compoundaccording to the present invention, the epoxy compound other than thecompound represented by the Formula (1), the oxetane compound and thevinyl ether, which are contained in the curable composition. When thecontent of the thermal cationic polymerization initiator is adjustedwithin the above described numerical range, the heat resistance of theresulting cured product can be improved to an even higher level.Further, the weight reduction of the cured product upon curing canfurther be decreased. In addition, the transparency of the cured productcan be further improved.

The thermal cationic polymerization initiator to be contained in thecurable composition according to the present invention is morepreferably selected from the group consisting of aromatic sulfoniumsalt-based thermal cationic polymerization initiators, aromatic iodoniumsalt-based thermal cationic polymerization initiators and aluminumcomplex-based thermal cationic polymerization initiators. Further, thethermal cationic polymerization initiator to be contained in the curablecomposition according to the present invention is still more preferablyan aromatic sulfonium salt-based thermal cationic polymerizationinitiator.

(2) Acid Anhydride-based Curing Agent

Examples of the acid anhydride-based curing agent to be contained in thecurable composition according to the present invention includehexahydrophthalic anhydride, methylhexahydrophthalic anhydride,tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride,endomethylenetetrahydrophthalic anhydride, methylnadic anhydride,methylbutenyltetrahydrophthalic anhydride, hydrogenated methylnadicanhydride, trialkyltetrahydrophthalic anhydride,cyclohexanetricarboxylic anhydride, methylcyclohexenedicarboxylicanhydride, methylcyclohexanetetracarboxylic acid dianhydride, maleicanhydride, phthalic anhydride, succinic anhydride, dodecenylsuccinicanhydride, octenylsuccinic anhydride, pyromellitic anhydride,trimellitic anhydride, alkylstyrene-maleic anhydride copolymer,chlorendic anhydride, polyazelaic anhydride, benzophenonetetracarboxylic anhydride, ethylene glycol bisanhydrotrimellitate,glycerol tristrimellitate, glycerin bis(anhydrotrimellitate)monoacetate, benzophenonetetracarboxylic acid, polyadipic anhydride,polysebacic anhydride, poly(ethyloctadecanedioic acid) anhydride,poly(phenylhexadecanedioic acid) anhydride, HET anhydride, andnorbornane-2,3-dicarboxylic anhydride.

Among these, hexahydrophthalic anhydride and methylhexahydrophthalicanhydride are preferred, because the combined use of any of these withthe composition according to the present invention or the epoxy compoundaccording to the present invention allows for improving the heatresistance and the transparency of the resulting cured product to aneven higher level. The curable composition according to the presentinvention can contain one kind, or two or more kinds of the acidanhydride-based curing agents described above.

From the viewpoint of improving the heat resistance of the resultingcured product, the content of the acid anhydride-based curing agent inthe curable composition according to the present invention, in caseswhere the curable composition does not contain the epoxy compound otherthan the compound represented by the Formula (1) to be described later,is preferably from 0.5 to 1.5 equivalents, more preferably from 0.6 to1.2 equivalents, and still more preferably from 0.8 to 1.2 equivalentswith respect to one epoxy equivalent of the composition according to thepresent invention or the epoxy compound according to the presentinvention contained in the curable composition. Further, in cases wherethe curable composition according to the present invention contains theepoxy compound other than the compound represented by the Formula (1),the content of the acid anhydride-based curing agent in the curablecomposition is preferably from 0.5 to 1.5 equivalents, more preferablyfrom 0.6 to 1.2 equivalents, and still more preferably from 0.8 to 1.2equivalents with respect to one epoxy equivalent of a mixture of epoxycompounds composed of the composition according to the present inventionor the epoxy compound according to the present invention and the epoxycompound other than the compound represented by the Formula (1), whichare contained in the curable composition.

(3) Curing Agent Other than Acid Anhydride-based Curing Agent

Examples of the curing agent which can be contained in the curablecomposition according to the present invention include, in addition tothe acid anhydride-based curing agents, amine-based curing agents,phenol-based curing agents and latent curing agents.

Examples of the amine-based curing agent include polyoxyethylenediamine, polyoxypropylene diamine, polyoxybutylene diamine,polyoxypentylene diamine, polyoxyethylene triamine, polyoxypropylenetriamine, polyoxybutylene triamine, polyoxypentylene triamine,diethylene triamine, triethylene tetramine, tetraethylene pentamine,m-xylene diamine, trimethylhexamethylene diamine, 2-methylpentamethylenediamine, diethylaminopropylamine, isophorone diamine,1,3-bisaminomethylcyclohexane, bis(4-aminocyclohexyl)methane, norbornanediamine, 1,2-diaminocyclohexane, diaminodiphenylmethane, metaphenylenediamine, diaminodiphenyl sulfone, and N-aminoethylpiperazine.

Examples of the phenol-based curing agent include xylyleneskeleton-containing phenol novolac resins, dicyclopentadieneskeleton-containing phenol novolac resins, biphenyl skeleton-containingphenol novolac resins, fluorene skeleton-containing phenol novolacresins, terpene skeleton-containing phenol novolac resins, bisphenol Anovolac, bisphenol F novolac, bisphenol S novolac, bisphenol AP novolac,bisphenol C novolac, bisphenol E novolac, bisphenol Z novolac, biphenolnovolac, tetramethyl bisphenol A novolac, dimethyl bisphenol A novolac,tetramethyl bisphenol F novolac, dimethyl bisphenol F novolac,tetramethyl bisphenol S novolac, dimethyl bisphenol S novolac,tetramethyl-4,4′-biphenol novolac, trishydroxyphenylmethane novolac,resorcinol novolac, hydroquinone novolac, pyrogallol novolac,diisopropylidene novolac, 1,1-di-4-hydroxyphenylfluorene novolac,phenolated polybutadiene novolac, phenol novolac, cresol novolac,ethylphenol novolac, butylphenol novolac, octylphenol novolac, andnaphthol novolac.

Examples of the latent curing agent include dicyandiamide, adipic aciddihydrazide, sebacic acid dihydrazide, dodecanedioic acid dihydrazide,isophthalic acid dihydrazide, ketimines, imidazole compounds,dihydrazide compounds, amine adduct-based latent curing agents. Thecurable composition according to the present invention may contain onekind, or two or more kinds of the curing agents as described above.

In a preferred embodiment of the curable composition according to thepresent invention, the curing agent is one or more curing agentsselected from the group consisting of acid anhydride-based curingagents, amine-based curing agents, phenol-based curing agents and latentcuring agents.

(4) Curing Accelerator

Examples of the curing accelerator to be contained in the curablecomposition according to the present invention include: phosphines andquaternary salts thereof, such as triphenylphosphine,triphenylbenzylphosphonium tetraphenylborate, tetrabutylphosphoniumdiethylphosphorodithioate, tetraphenylphosphonium bromide,tetrabutylphosphonium acetate, tetra-n-butylphosphonium bromide,tetra-n-butylphosphonium benzotriazolate, tetra-n-butylphosphoniumtetrafluoroborate, tetra-n-butylphosphonium tetraphenylborate,methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide,ethyltriphenylphosphonium iodide, ethyltriphenylphosphonium acetate,methyltri-n-butylphosphonium dimethylphosphate,n-butyltriphenylphosphonium bromide, benzyltriphenylphosphoniumchloride, and tetraphenylphosphonium tetraphenylborate; imidazoles suchas 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole,1-benzyl-2-phenylimidazole, 2-methylimidazole, 2-phenylimidazole,1-(2-cyanoethyl)-2-ethyl-4-methylimidazole,2,4-diamino-6-[2-methylimidazolyl-(1)]ethyl-s-triazine,2-phenylimidazoline, and 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole;tertiary amines and quaternary salts thereof such as,tris(dimethylaminomethyl)phenol, benzyldimethylamine, andtetrabutylammonium bromide; super strong basic organic compounds such as1,8-diazabicyclo(5,4,0)undecene-7 and 1,5-diazabicyclo(4,3,0)nonene-5;organic metal carboxylates such as zinc octylate, zinc laurate, zincstearate, and tin octylate; metal-organic chelate compounds such asbenzoylacetone zinc chelate, dibenzoylmethane zinc chelate and ethylacetoacetate zinc chelate; and tetra-n-butylsulfonium-o,o-diethylphosphorodithionate.

Among these, an imidazole-based curing accelerator is particularlypreferred, because the combined use thereof with the compositionaccording to the present invention or the epoxy compound according tothe present invention allows for improving the heat resistance of theresulting cured product to an even higher level.

The curable composition according to the present invention may containone kind, or two or more kinds of the curing accelerators as describedabove.

From the viewpoint of improving the heat resistance of the resultingcured product, the content of the curing accelerator in the curablecomposition according to the present invention, in cases where thecurable composition does not contain the epoxy compound other than thecompound represented by the Formula (1) to be described later, ispreferably from 0.1 to 10 parts by mass, more preferably from 0.2 to 8parts by mass, and still more preferably from 0.5 to 6 parts by masswith respect to 100 parts by mass of the composition according to thepresent invention or the epoxy compound according to the presentinvention contained in the curable composition. Further, in cases wherethe curable composition according to the present invention contains theepoxy compound other than the compound represented by the Formula (1),the content of the curing accelerator in the curable composition ispreferably from 0.1 to 10 parts by mass, more preferably from 0.2 to 8parts by mass, and still more preferably from 0.5 to 6 parts by masswith respect to 100 parts by mass of the total amount of the compositionaccording to the present invention or the epoxy compound according tothe present invention and the epoxy compound other than the compoundrepresented by the Formula (1), which are contained in the curablecomposition.

(5) Photo-cationic Polymerization Initiator

The photo-cationic polymerization initiator to be contained in thecurable composition according to the present invention is one whichgenerates cationic species or Lewis acid when irradiated with an activeenergy ray such as a visible ray, UV light, an X ray or an electronbeam, thereby initiating a polymerization reaction of a cationicallypolymerizable compound. As the photo-cationic polymerization initiatorto be contained in the curable composition according to the presentinvention, it is possible to use, for example, a compound such as anonium salt, a metallocene complex, or an iron-allene complex. Examplesof the onium salt which can be used include aromatic sulfonium salts,aromatic iodonium salts, aromatic diazonium salts, aromatic phosphoniumsalts and aromatic selenium salts. As the counter ions for these salts,anions such as CF₃SO₃ ⁻, BF₄ ⁻, PF₆ ⁻, AsF₆ ⁻, and SbF₆ ⁻ are used.Among these, it is more preferred to use an aromatic sulfoniumsalt-based photo-cationic polymerization initiator, since it exhibits anexcellent curing performance due to having UV absorption properties evenin the wavelength range of 300 nm or more, and allows for providing acured product having a good mechanical strength and adhesion strength.The curable composition according to the present invention may containtwo or more kinds of the photo-cationic polymerization initiators.

Examples of the aromatic sulfonium salt includediphenyl-4-(phenylthio)phenylsulfonium hexafluorophosphate,4,4′-bis(diphenylsulfonio)diphenylsulfide bishexafluorophosphate,4,4′-bis[di(β-hydroxyethoxy)phenylsulfonio]diphenylsulfidebishexafluoroantimonate,4,4′-bis[di(β-hydroxyethoxy)phenylsulfonio]diphenylsulfidebishexafluorophosphate, 7-[di(p-toluyl)sulfonio]-2-isopropylthioxanthonehexafluoroantimonate, 7-[di(p-toluyl)sulfonio]-2-isopropylthioxanthonetetrakis(pentafluorophenyl)borate,4-phenylcarbonyl-4′-diphenylsulfonio-diphenylsulfidehexafluorophosphate,4-(p-tert-butylphenylcarbonyl)-4′-diphenylsulfonio-diphenylsulfidehexafluoroantimonate,4-(p-tert-butylphenylcarbonyl)-4′-di(p-toluyl)sulfonio-diphenylsulfidetetrakis(pentafluorophenyl)borate,diphenyl-4-(phenylthio)phenylsulfonium hexafluoroantimonate,triphenylsulfonium trifluoromethanesulfonate,bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluoroantimonate, and(4-methoxyphenyl)diphenylsulfonium hexafluoroantimonate.

Examples of the aromatic iodonium salt include diphenyliodoniumtetrakis(pentafluorophenyl)borate, diphenyliodonium hexafluorophosphate,diphenyliodonium hexafluoroantimonate, di(4-nonylphenyl)iodoniumhexafluorophosphate, (4-methoxyphenyl)phenyliodoniumhexafluoroantimonate, and bis(4-t-butylphenyl)iodoniumhexafluorophosphate.

Examples of the aromatic diazonium salt include benzenediazoniumhexafluoroantimonate, benzenediazonium hexafluorophosphate,benzenediazonium tetrafluoroborate, and 4-chlorobenzenediazoniumhexafluorophosphate.

Examples of the aromatic phosphonium salt includebenzyltriphenylphosphonium hexafluoroantimonate.

Examples of the aromatic selenium salt include triphenylseleniumhexafluorophosphate.

Examples of the iron-allene complex include xylene-cyclopentadienyl iron(II) hexafluoroantimonate, cumene-cyclopentadienyl iron (II)hexafluorophosphate, and xylene-cyclopentadienyl iron (II)tris(trifluoromethylsulfonyl)methanide.

In cases where the curable composition according to the presentinvention does not contain any of the epoxy compound other than thecompound represented by the Formula (1) to be described later, theoxetane compound to be described later, and the vinyl ether to bedescribed later, the content of the photo-cationic polymerizationinitiator in the curable composition is preferably from 0.1 to 20 partsby mass, and more preferably from 0.3 to 15 parts by mass with respectto 100 parts by mass of the composition according to the presentinvention or the epoxy compound according to the present inventioncontained in the curable composition. Further, in cases where thecurable composition according to the present invention contains onekind, or two or more kinds selected from the group consisting of theepoxy compound other than the compound represented by the Formula (1),the oxetane compound and the vinyl ether, the content of thephoto-cationic polymerization initiator in the curable composition ispreferably from 0.1 to 20 parts by mass, and more preferably from 0.3 to15 parts by mass with respect to 100 parts by mass of the total amountof the composition according to the present invention or the epoxycompound according to the present invention, the epoxy compound otherthan the compound represented by the Formula (1), the oxetane compoundand the vinyl ether, which are contained in the curable composition.When the content of the photo-cationic polymerization initiator isadjusted within the above described numerical range, the heat resistanceof the resulting cured product can be improved to an even higher level.In addition, the transparency of the cured product can further beimproved.

(6) Epoxy Compound Other than Compound Represented by the Formula (1)

The curable composition according to the present invention may containan epoxy compound other than the compound represented by the Formula (1)(in the present specification, sometimes also referred to as “the otherepoxy compound”), depending on the application. Examples of the epoxycompound other than the compound represented by the Formula (1) includeglycidyl ether-type epoxides, glycidyl ester-type epoxides, glycidylamine-type epoxides and alicyclic epoxides; as well as oligomers andpolymers thereof.

Examples of the glycidyl ether-type epoxide include: glycidyl ethers ofdivalent phenols such as bisphenol A diglycidyl ether, bisphenol Fdiglycidyl ether, bisphenol S diglycidyl ether, tetramethyl biphenoldiglycidyl ether, hydrogenated bisphenol A diglycidyl ether, andbrominated bisphenol A diglycidyl ether; glycidyl ethers of polyvalentphenols such as dihydroxynaphthyl cresol triglycidyl ether,tris(hydroxyphenyl)methane triglycidyl ether,tetrakis(hydroxyphenyl)ethane tetraglycidyl ether, dinaphthyltrioltriglycidyl ether, phenol novolac glycidyl ether, cresol novolacglycidyl ether, xylylene skeleton-containing phenol novolac glycidylethers, dicyclopentadiene skeleton-containing phenol novolac glycidylethers, biphenyl skeleton-containing phenol novolac glycidyl ethers,terpene skeleton-containing phenol novolac glycidyl ethers, bisphenol Anovolac glycidyl ether, bisphenol F novolac glycidyl ether, bisphenol Snovolac glycidyl ether, bisphenol AP novolac glycidyl ether, bisphenol Cnovolac glycidyl ether, bisphenol E novolac glycidyl ether, bisphenol Znovolac glycidyl ether, biphenol novolac glycidyl ether, tetramethylbisphenol A novolac glycidyl ether, dimethyl bisphenol A novolacglycidyl ether, tetramethyl bisphenol F novolac glycidyl ether, dimethylbisphenol F novolac glycidyl ether, tetramethyl bisphenol S novolacglycidyl ether, dimethyl bisphenol S novolac glycidyl ether,tetramethyl-4,4′-biphenol novolac glycidyl ether,trishydroxyphenylmethane novolac glycidyl ether, resorcinol novolacglycidyl ether, hydroquinone novolac glycidyl ether, pyrogallol novolacglycidyl ether, diisopropylidene novolac glycidyl ether,1,1-di-4-hydroxyphenylfluorene novolac glycidyl ether, phenolatedpolybutadiene novolac glycidyl ether, ethylphenol novolac glycidylether, butylphenol novolac glycidyl ether, octylphenol novolac glycidylether, naphthol novolac glycidyl ether, and hydrogenated phenol novolacglycidyl ether; glycidyl ethers of divalent alcohols such as ethyleneglycol diglycidyl ether, propylene glycol diglycidyl ether,tetramethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether,cyclohexanedimethylol diglycidyl ether, polyethylene glycol diglycidylether, and polypropylene glycol diglycidyl ether; glycidyl ethers ofpolyols such as trimethylolpropane triglycidyl ether, glycerintriglycidyl ether, pentaerythritol tetraglycidyl ether, sorbitolhexaglycidyl ether, and polyglycerin polyglycidyl ether; and triglycidylisocyanurate.

Examples of the glycidyl ester-type epoxide include: glycidyl esters ofcarboxylic acids such as glycidyl methacrylate, phthalic acid diglycidylester, isophthalic acid diglycidyl ester, terephthalic acid diglycidylester, cyclohexanedicarboxylic acid diglycidyl ester, and trimelliticacid triglycidyl ester; and glycidyl ester-type polyepoxides.

Examples of the glycidyl amine-type epoxide include: glycidyl aromaticamines such as N,N-diglycidylaniline, N,N-diglycidyltoluidine,N,N,N′,N′-tetraglycidyldiaminodiphenylmethane,N,N,N′,N′-tetraglycidyldiaminodiphenylsulfone, andN,N,N′,N′-tetraglycidyldiethyldiphenylmethane; and glycidyl heterocyclicamines such as bis(N,N-diglycidylaminocyclohexyl)methane (hydride ofN,N,N′,N′-tetraglycidyldiaminodiphenylmethane),N,N,N′,N′-tetraglycidyl-1,3-(bisaminomethyl)cyclohexane (hydride ofN,N,N′,N′-tetraglycidylxylylene diamine), trisglycidylmelamine,triglycidyl-p-aminophenol, N-glycidyl-4-glycidyloxypyrrolidone.

Examples of the alicyclic epoxide include vinyl cyclohexene dioxide,limonene dioxide, dicyclopentadiene dioxide, bis(2,3-epoxycyclopentyl)ether, ethylene glycol bisepoxy dicyclopentyl ether,3,4-epoxy-6-methylcyclohexylmethyl 3′,4′-epoxy-6′-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate,3,4-epoxy-1-methylcyclohexyl 3,4-epoxy-1-methylhexane carboxylate,3,4-epoxy-3-methylcyclohexylmethyl 3,4-epoxy-3-methylhexane carboxylate,3,4-epoxy-5-methylcyclohexylmethyl 3,4-epoxy-5-methylcyclohexanecarboxylate,2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-metadioxane,methylenebis(3,4-epoxycyclohexane), (3,3′,4,4′-diepoxy)bicyclohexyl,1,2-epoxy-(2-oxiranyl)cyclohexane adduct of2,2-bis(hydroxymethyl)-1-butanol, and tetrahydroindene diepoxide. Thecurable composition according to the present invention may contain onekind, or two or more kinds of epoxy compounds other than the compoundrepresented by the Formula (1), such as those as described above.

The content of the above described epoxy compound other than thecompound represented by the Formula (1) is preferably from 1 to 90% bymass, and more preferably from 5 to 85% by mass with respect to theamount of curable composition, from the viewpoint of improving the heatresistance of the resulting cured product.

In one preferred embodiment, the epoxy compound other than the compoundrepresented by the Formula (1), which is contained in the curablecomposition according to the present invention, is selected from thegroup consisting of glycidyl ether-type epoxides, glycidyl ester-typeepoxides and alicyclic epoxides.

(7) Reactive Diluent

The curable composition according to the present invention may furthercontain a reactive diluent in order to reduce the viscosity. Examples ofthe reactive diluent include a monoepoxy compound produced by the methoddescribed in Preparation Example 6, butyl glycidyl ether, 2-ethylhexylglycidyl ether, glycidyl ether of a mixture of C12 and C13 alcohols, and1,2-epoxy-4-vinylcyclohexane. The curable composition may contain onekind, or two or more kinds of the reactive diluents as described above.The mixing ratio of the reactive diluent may be adjusted as appropriatesuch that the curable composition containing the reactive diluent has adesired viscosity.

(8) Oxetane Compound

The curable composition according to the present invention may containan oxetane compound. Examples of the oxetane compound include1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene,3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3-(phenoxymethyl)oxetane,di[(3-ethyl-3-oxetanyl)methyl] ether,3-ethyl-3-(2-ethylhexyloxymethyl)oxetane,3-ethyl-3-(cyclohexyloxymethyl)oxetane, phenol novolac oxetane,1,3-bis[(3-ethyloxetan-3-yl)]methoxybenzene, oxetanyl silsesquioxane,oxetanyl silicate, bis[1-ethyl(3-oxetanyl)]methyl ether,4,4′-bis[(3-ethyl-3-oxetanyl)methoxymethyl]biphenyl,4,4′-bis(3-ethyl-3-oxetanylmethoxy)biphenyl, ethylene glycol(3-ethyl-3-oxetanylmethyl) ether, diethylene glycolbis(3-ethyl-3-oxetanylmethyl) ether, bis(3-ethyl-3-oxetanylmethyl)diphenoate, trimethylolpropane propane tris(3-ethyl-3-oxetanylmethyl)ether, pentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, andphenol novolac-type oxetane compounds. The curable composition accordingto the present invention may contain one kind, or two or more kinds ofthe oxetane compounds as described above.

The content of the oxetane compound in the curable composition accordingto the present invention is preferably from 1 to 90% by mass, and morepreferably from 5 to 85% by mass, from the viewpoint of improving theheat resistance of the resulting cured product.

(9) Vinyl Ether Compound

The curable composition according to the present invention may contain avinyl ether compound. Examples of the vinyl ether compound include:monofunctional vinyl ethers such as methyl vinyl ether, ethyl vinylether, propyl vinyl ether, and butyl vinyl ether; polyfunctional vinylethers such as ethylene glycol divinyl ether, butanediol divinyl ether,cyclohexanedimethanol divinyl ether, cyclohexanediol divinyl ether,trimethylolpropane trivinyl ether, pentaerythritol tetravinyl ether,glycerol trivinyl ether, triethylene glycol divinyl ether, anddiethylene glycol divinyl ether; vinyl ether compounds containing ahydroxyl group such as hydroxyethyl vinyl ether, hydroxybutyl vinylether, cyclohexanedimethanol monovinyl ether, cyclohexanediol monovinylether, 9-hydroxynonyl vinyl ether, propylene glycol monovinyl ether,neopentyl glycol monovinyl ether, glycerol divinyl ether, glycerolmonovinyl ether, trimethylolpropane divinyl ether, trimethylolpropanemonovinyl ether, pentaerythritol monovinyl ether, pentaerythritoldivinyl ether, pentaerythritol trivinyl ether, diethylene glycolmonovinyl ether, triethylene glycol monovinyl ether, tetraethyleneglycol monovinyl ether, tricyclodecanediol monovinyl ether, andtricyclodecane dimethanol monovinyl ether; and vinyl ethers containingdifferent types of functional groups, such as 2-(2-vinyloxyethoxy)ethylacrylate, and 2-(2-vinyloxyethoxy)ethyl methacrylate. The curablecomposition according to the present invention may contain one kind, ortwo or more kinds of the vinyl ether compounds as described above.

The content of the vinyl ether compound in the curable compositionaccording to the present invention is preferably from 1 to 90% by mass,and more preferably from 5 to 85% by mass, from the viewpoint ofimproving the heat resistance of the resulting cured product.

(10) Compound Containing Hydroxyl Group

The curable composition according to the present invention may furthercontain a compound containing a hydroxyl group. Incorporation of acompound containing a hydroxyl group into the curable composition allowsa moderate curing reaction to proceed. Examples of the compoundcontaining a hydroxyl group include ethylene glycol, diethylene glycol,and glycerin. The curable composition according to the present inventionmay contain one kind, or two or more kinds of the compounds containing ahydroxyl group, such as those described above.

The content of the compound containing a hydroxyl group in the curablecomposition according to the present invention is preferably from 0.1 to10% by mass, and more preferably from 0.2 to 8% by mass, from theviewpoint of improving the heat resistance of the resulting curedproduct.

(11) Other Components

The curable composition according to the present invention may furthercontain a solvent. Examples of the solvent include methyl ethyl ketone,ethyl acetate, toluene, methanol, and ethanol.

The curable composition according to the present invention may containvarious types of additives to the extent that the properties of thecomposition are not impaired. Examples of the additives include fillers,silane coupling agents, mold release agents, coloring agents, flameretardants, antioxidants, photostabilizers and plasticizers, antifoamingagents, photostabilizers, coloring agents such as pigments and dyes,plasticizers, pH adjusting agents, coloration inhibitors, mattingagents, deodorants, weather resistant agents, antistatic agents, yarnfriction reducing agents, slip agents, and ion exchangers.

(12) Production of Curable Composition

The curable composition according to the present invention can beproduced in accordance with technical common knowledge widely known tothose skilled in the art, and the method of producing the curablecomposition and the components to be further included in the curablecomposition can be selected as appropriate.

4. Cured Product

(1) Conditions for Curing

The cured product according to the present invention is obtained bycuring the above described curable composition according to the presentinvention. The method of curing the curable composition is notparticularly limited, and the composition can be cured by heating orirradiation of light, as appropriate.

In cases where the curable composition is cured by heating, the heatingof the curable composition is preferably carried out in multiple stages,taking into consideration the degree of reactivity of the epoxycompound. This allows for a sufficient curing reaction to proceed. Forexample, the curing reaction can be carried out by performing a firstheating at a temperature of from 100 to 130° C. for 10 to 150 minutes, asecond heating at 140 to 160° C. for 10 to 150 minutes, a third heatingat 170 to 200° C. for 60 to 180 minutes, and a fourth heating at 210 to250° C. for 10 to 150 minutes. Alternatively, the curing reaction canalso be carried out, for example, by performing a first heating at atemperature of from 100 to 130° C. for 10 to 150 minutes, a secondheating at 140 to 200° C. for 10 to 150 minutes, and a third heating at210 to 250° C. for 10 to 150 minutes. Still alternatively, the curingreaction can also be carried out, for example, by performing a firstheating at a temperature of from 80 to 100° C. for 10 to 150 minutes, asecond heating at 110 to 120° C. for 10 to 150 minutes, a third heatingat 130 to 140° C. for 60 to 180 minutes, a fourth heating at 150 to 170°C. for 10 to 150 minutes, a fifth heating at 180 to 200° C. for 60 to180 minutes and a sixth heating at 210 to 230° C. for 60 to 240 minutes.Still alternatively, the curing reaction can be carried out, forexample, by performing a first heating at a temperature of from 100 to110° C. for 10 to 150 minutes, a second heating at 120 to 150° C. for 10to 150 minutes, a third heating at 160 to 220° C. for 10 to 150 minutes,and a fourth heating at 230 to 250° C. for 10 to 150 minutes. However,the heating conditions are not limited to those described above, and theheating is preferably carried out varying the conditions as appropriate,in view of the content of the epoxy compound and the properties of othercompounds and the like contained in the curable composition.

In cases where the curable composition is cured by the irradiation of anactive energy ray, such as a visible ray, UV light, an X ray or anelectron beam, the type of the active energy ray used and the conditionsfor irradiation are preferably selected as appropriate, depending on thecomposition of the curable composition. In one embodiment, it ispreferred that the irradiation of UV light be carried out such that theaccumulated amount of light, which is represented as the product of theirradiation intensity and the irradiation time, is adjusted within therange of from 10 to 5,000 mJ/cm². When the accumulated amount of lightirradiated to the curable composition is adjusted within the abovedescribed numerical range, it is possible to allow active speciesderived from the photo-cationic polymerization initiator to be generatedsufficiently. This also allows for an improvement in the productivity.

(2) Applications of Cured Product

Specific examples of the application of the curable compositionaccording to the present invention and the cured product obtainedtherefrom include: coating materials for coating on substrates such asmetals, resin films, glass, paper and wood, surface protective films forsemiconductor devices and organic thin film elements (for example,organic electroluminescent elements and organic thin film solar cellelements), hard coating agents, anti-fouling films and antireflectionfilms; adhesive agents, tacky materials; various types of opticalmembers such as lenses, prisms, filters, image display materials, lensarrays, sealing materials and reflector materials for opticalsemiconductor devices, sealing materials for semiconductor devices,optical waveguides, light guide plates, light diffusion plates,diffraction elements and optical adhesive agents; and materials such ascasting materials, interlayer insulators, insulating films for printedalignment substrates and fiber-reinforced composite materials.

EXAMPLES

The present invention will now be described in further detail by way ofExamples. However, the present invention is in no way limited by theseExamples.

1. Preparation Example 1: Preparation of Composition (A-1)

Into a reaction vessel equipped with a thermometer, an agitator, areflux tube and a dropping device, 559 g of a diolefin compoundrepresented by the following Formula (4), 840 g of toluene, and 25 g ofsodium acetate were charged. To the reactor, 1,219 g of a 38% aqueoussolution of peracetic acid was added dropwise over eight hours, whilestirring at room temperature. The stirring was continued at roomtemperature for 17 hours, followed by stirring at 30° C. for two hours.

Subsequently, a 10% aqueous solution of sodium sulfite, a 20% aqueoussolution of NaOH, and water were used to carry out washing. Theresulting solution was concentrated with a rotary evaporator.Thereafter, the resultant was dissolved in isopropyl alcohol whileheating at 63° C., and then cooled to −10° C. to allow crystallizationto occur, followed by collecting solids by filtration. The solidscollected by filtration were washed with 150 mL of isopropyl alcohol,and then dried to obtain 394 g of a composition (A-1) as white solids.

The resulting composition (A-1) was analyzed by gas chromatography underthe following analysis conditions. FIG. 1 shows a gas chromatograph ofthe composition (A-1). As shown in FIG. 1, peaks derived from thestereoisomers of the compound represented by Formula (1) were observedwithin the range of retention time of from 27.5 to 29.0 minutes. Asshown in FIG. 1, the ratio of the area of the maximum peak within therange of retention time of from 27.6 to 28.0 minutes with respect to thetotal area of peaks within the range of retention time of from 27.5 to29.0 minutes was 84%.

(Analysis Conditions)

Measurement apparatus: Agilent 6850 series, manufactured by AgilentTechnologies Inc.

Column: HP-1 (manufactured by Agilent Technologies Inc.),dimethylpolysiloxane, length: 60.0 m, inner diameter: 250 μm, filmthickness: 0.25 μm

Carrier gas: N₂

Flow velocity: 1.3 mL/min

Sample inlet temperature: 140° C.

Detector temperature: 250° C.

Sample injection volume: 0.2 μL

Temperature increase conditions: 80° C. (3 min), 80 to 150° C. (10°C./min), 150 to 250° C. (5° C./min), 250° C. (20 min)

2. Preparation Example 2: Preparation of Composition (A-2)

A quantity of 10.0 g of the composition (A-1) was dissolved in isopropylalcohol at 60° C., and cooled to 25° C. to allow crystallization tooccur, followed by collecting solids by filtration. The solids collectedby filtration were washed with 15 mL of isopropyl alcohol, and thendried to obtain 6.63 g of a composition (A-2).

The resulting composition (A-2) was analyzed by gas chromatography underthe analysis conditions described in Preparation Example 1. FIG. 2 showsa gas chromatograph of the composition (A-2). As shown in FIG. 2, peaksderived from the stereoisomers of the compound represented by Formula(1) were observed within the range of retention time of from 27.5 to29.0 minutes. As shown in FIG. 2, the ratio of the area of the maximumpeak within the range of retention time of from 27.6 to 28.0 minuteswith respect to the total area of peaks within the range of retentiontime of from 27.5 to 29.0 minutes was 91%.

3. Preparation Example 3: Preparation of Composition (A-3)

A quantity of 3.65 g of mother liquor concentrate which had beenobtained when filtering the composition (A-1) in the crystallizationoperation in the procedure of preparing the composition (A-1), waspurified by silica gel column chromatography, to obtain 2.25 g of acomposition (A-3).

The resulting composition (A-3) was analyzed by gas chromatography underthe analysis conditions described in Preparation Example 1. FIG. 3 showsa gas chromatograph of the composition (A-3). As shown in FIG. 3, peaksderived from the stereoisomers of the compound represented by Formula(1) were observed within the range of retention time of from 27.5 to29.0 minutes. As shown in FIG. 3, the ratio of the area of the maximumpeak within the range of retention time of from 27.6 to 28.0 minuteswith respect to the total area of peaks within the range of retentiontime of from 27.5 to 29.0 minutes was 36%.

4. Preparation Example 4: Preparation of Composition (A-4)

Into a reaction vessel equipped with a thermometer, an agitator, areflux tube and a dropping device, 4.3 g of 35% hydrogen peroxide and0.30 g of H₃PW₁₂O₄₀ were charged, followed by stirring at 60° C. for 30minutes. After cooling the resultant to 40° C., 36.2 g of the diolefincompound represented by the above described Formula (4), 0.11 g ofcetylpyridinium chloride, and 252 g of chloroform were added thereto.Subsequently, 38.9 g of 35% hydrogen peroxide was added dropwise whilestirring at 40° C., and a reaction was allowed proceed at 40° C. for sixhours.

After the completion of the reaction, 180 g of chloroform was used tocarry out a separation and extraction operation. The organic layer waswashed with 120 mL of a 10% aqueous solution of sodium thiosulfate, 120mL of a 10% aqueous solution of sodium carbonate, and 120 mL of purewater. After carrying out a dehydration operation with sodium sulfate, arotary evaporator was used to remove the solvent contained therein bydistillation. The resultant was then subjected to distillation at apressure of 2 hPa and at a bottom temperature of from 180 to 200° C., toobtain 6.0 g of a composition (A-4), which is a composition of interest,at a bottom temperature 195° C.

The resulting composition (A-4) was analyzed by gas chromatography underthe analysis conditions described in Preparation Example 1. FIG. 4 showsa gas chromatograph of the composition (A-4). As shown in FIG. 4, peaksderived from the stereoisomers of the compound represented by Formula(1) were observed within the range of retention time of from 27.5 to29.0 minutes. As shown in FIG. 4, the ratio of the area of the maximumpeak within the range of retention time of from 27.6 to 28.0 minuteswith respect to the total area of peaks within the range of retentiontime of from 27.5 to 29.0 minutes was 62%.

5. Example 1: Preparation of Curable Compositions ContainingCompositions (A-1 to A-4) and Evaluation Thereof (1) Example 1-1

Production of Curable Composition

The composition (A-2) obtained by the method described in PreparationExample 2 and a thermal cationic polymerization initiator were mixed toachieve the following composition, to obtain a curable composition.

<Composition of Curable Composition>

Composition (A-2) 100 parts by mass (the composition obtained by themethod described in the Preparation Example 2)

Thermal cationic polymerization initiator 2 parts by mass (an aromaticsulfonium salt: 4-acetoxyphenyldimethylsulfonium hexafluoroantimonate,manufactured by Sanshin Chemical Industry Co., Ltd., trade name:SI-150L)

(2) Example 1-2

A curable composition was obtained in the same manner as in Example 1-1,except that the composition (A-1) (the composition obtained by themethod described in the Preparation Example 1) was used instead of thecomposition (A-2).

(3) Example 1-3

A curable composition was obtained in the same manner as in Example 1-1,except that the composition (A-4) (the composition obtained by themethod described in the Preparation Example 4) was used instead of thecomposition (A-2).

(4) Reference Example 1-1

A curable composition was obtained in the same manner as in Example 1-1,except that the composition (A-3) (the composition obtained by themethod described in the Preparation Example 3) was used instead of thecomposition (A-2).

<Evaluation of Physical Properties>

The curable compositions obtained in the Examples and Reference Examplewere heated in a hot air circulating oven at 130° C. for one hour, at150° C. for one hour, at 180° C. for two hours, and then at 220° C. forthree hours, to obtain cured products.

The glass transition temperature of each of the thus obtained curedproducts was measured by increasing the temperature from 30 to 300° C.at a rate of 10° C./min, using a differential scanning calorimeter,DSC7020, manufactured by SII NanoTechnology Inc., and the thus measuredvalue was taken as the heat resistance of the cured product. The glasstransition temperature as used herein refers to a value measured inaccordance with JIS K7121, based on “Midpoint Glass TransitionTemperature: T_(mg)” described in the section of “Method for MeasuringTransition Temperature of Plastics”. The measurement results aresummarized in Table 1.

TABLE 1 Ex- Reference Example Example ample Example 1-1 1-2 1-3 1-1Composition Composition 100 of curable (A-2) resin Composition 100composition (A-1) (parts by Composition 100 mass) (A-4) Composition 100(A-3) Thermal 2 2 2 2 cationic poly- merization initiator Heatresistance (° C.) 250 248 245 241

6. Preparation Example 5: Preparation of Composition (A-5)

A quantity of 1.02 g of the composition (A-2) was dissolved in isopropylalcohol at 60° C., and cooled to 25° C. to allow crystallization tooccur, followed by collecting solids by filtration. The solids collectedby filtration were washed with 5 mL of isopropyl alcohol, and then driedto obtain 0.500 g of a composition (A-5).

The resulting composition (A-5) was analyzed by gas chromatography underthe analysis conditions described in Preparation Example 1. FIG. 5 showsa gas chromatograph of the composition (A-5). As shown in FIG. 5, peaksderived from the stereoisomers of the compound represented by Formula(1) were observed within the range of retention time of from 27.5 to29.0 minutes. As shown in FIG. 5, the ratio of the area of the maximumpeak within the range of retention time of from 27.6 to 28.0 minuteswith respect to the total area of peaks within the range of retentiontime of from 27.5 to 29.0 minutes was 96%.

The stereoisomeric structure of the resulting composition (A-5) wasidentified by ¹H-NMR and ¹³C-NMR.

A chart showing ¹H NMR peaks of the composition (A-5) is shown in FIG.6, and a chart showing ¹³C NMR peaks of the composition (A-5) is shownin FIG. 7. Based on the results of these NMR analyses and the abovedescribed chromatography analysis, it is thought that the mother nucleusstructure of a compound represented by the maximum peak in thecomposition (A-5) has a steric configuration represented by thefollowing Formula (5):

7. Preparation Example 6: Production of Monoepoxy Compound as ReactiveDiluent Production Example of Monoepoxy Compound

Into a reaction vessel equipped with a thermometer, an agitator, areflux tube and a dropping device, 3,132 g of the diolefin compoundrepresented by the following Formula (6), 3,132 g of toluene and sodiumacetate were charged. To the reactor, 3,783 g of a 38% aqueous solutionof peracetic acid was added dropwise over five hours, while stirring at−5° C. While continuing to stir the mixture at −5° C., a reaction wasallowed to proceed for 17 hours.

Subsequently, a 10% aqueous solution of sodium sulfite was used to carryout a neutralization treatment, followed by a liquid separationoperation. The resultant was then subjected to distillation at apressure of 2 hPa and at a bottom temperature of from 130 to 140° C., toobtain 2,109 g of a colorless transparent liquid. In the ¹³C-NMRspectrum and the precise mass measurement by LC-MS, the [M+H]+ of thethus obtained liquid was determined to be 191.1439, which corresponds tothe theoretical structure. Accordingly, it was confirmed that theresulting liquid was a monoepoxy compound of interest satisfying thefollowing Formula (7). The viscosity of the resulting monoepoxy compoundwas measured using a Type E viscometer, to be 11.0 mPa·s.

The invention claimed is:
 1. A composition comprising at least one ormore stereoisomers of a compound represented by the following Formula(1):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group)wherein, in a gas chromatogram obtained by analyzing the composition bygas chromatography under the following analysis conditions, the ratio ofthe area of the maximum peak with respect to the total area of peaksderived from the stereoisomers is 60% or more, wherein the maximum peakis present within the range of retention time of from 27.6 to 28.0minutes, and wherein the analysis conditions are as follows: column:HP-1 (manufactured by Agilent Technologies Inc.), length: 60.0 m, innerdiameter: 250 μm, film thickness: 0.25 μm; liquid phase: 100%dimethylpolysiloxane; carrier gas: N₂; flow velocity: 1.3 mL/min; sampleinlet temperature: 140° C.; detector temperature: 250° C.; sampleinjection volume: 0.2 μL; and temperature increase conditions: 80° C. (3min), 80 to 150° C. (10° C./min), 150 to 250° C. (5° C./min), 250° C.(20 min).
 2. A composition comprising at least one or more stereoisomersof a compound represented by the following Formula (1):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group)wherein, in a gas chromatogram obtained by analyzing the composition bygas chromatography under the following analysis conditions, the ratio ofthe area of the maximum peak within the range of retention time of from27.6 to 28.0 minutes with respect to the total area of peaks within therange of retention time of from 27.5 to 29.0 minutes is 60% or more, andwherein the analysis conditions are as follows: column: HP-1(manufactured by Agilent Technologies Inc.), length: 60.0 m, innerdiameter: 250 μm, film thickness: 0.25 μm; liquid phase: 100%dimethylpolysiloxane; carrier gas: N₂; flow velocity: 1.3 mL/min; sampleinlet temperature: 140° C.; detector temperature: 250° C.; sampleinjection volume: 0.2 μL; and temperature increase conditions: 80° C. (3min), 80 to 150° C. (10° C./min), 150 to 250° C. (5° C./min), 250° C.(20 min).
 3. The composition according to claim 1, wherein the compoundrepresented by the Formula (1) is a reaction product of a compoundrepresented by the following Formula (2):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group) witha peracid.
 4. The composition according to claim 1, wherein the maximumpeak is the first peak among the peaks derived from the stereoisomers.5. The composition according to claim 1, wherein the maximum peak is thefirst peak appearing after a retention time of 27.5 minutes, among thepeaks within the range of retention time of from 27.5 to 29.0 minutes.6. The composition according to claim 1, wherein the R¹ to R¹⁸ are allhydrogen atoms.
 7. The composition according to claim 1, wherein thestereoisomer corresponding to the maximum peak is represented by thefollowing Formula (3):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group). 8.An epoxy compound represented by the following Formula (3):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group),wherein, in a gas chromatogram obtained by analyzing the composition bygas chromatography under the following analysis conditions, the ratio ofthe area of the maximum peak with respect to the total area of peaksderived from the stereoisomers is 60% or more, wherein the maximum peakis present within the range of retention time of from 27.6 to 28.0minutes, and wherein the analysis conditions are as follows: column:HP-1 (manufactured by Agilent Technologies Inc.), length: 60.0 m, innerdiameter: 250 μm, film thickness: 0.25 μm; liquid phase: 100%dimethylpolysiloxane; carrier gas: N₂; flow velocity: 1.3 mL/min; sampleinlet temperature: 140° C.; detector temperature: 250° C.; sampleinjection volume: 0.2 μL; and temperature increase conditions: 80° C. (3min), 80 to 150° C. (10° C./min), 150 to 250° C. (5° C./min), 250° C.(20 min).
 9. A curable composition comprising: the epoxy compositionaccording to claim 1 or an epoxy compound represented by the followingFormula (3):

(wherein R¹ to R¹⁸ are each independently selected from the groupconsisting of a hydrogen atom, an alkyl group and an alkoxy group),wherein, in a gas chromatogram obtained by analyzing the composition bygas chromatography under the following analysis conditions, the ratio ofthe area of the maximum peak with respect to the total area of peaksderived from the stereoisomers is 60% or more, wherein the maximum peakis present within the range of retention time of from 27.6 to 28.0minutes, and wherein the analysis conditions are as follows: column:HP-1 (manufactured by Agilent Technologies Inc.), length: 60.0 m, innerdiameter: 250 μm, film thickness: 0.25 μm; liquid phase: 100%dimethylpolysiloxane; carrier gas: N₂; flow velocity: 1.3 mL/min; sampleinlet temperature: 140° C.; detector temperature: 250° C.; sampleinjection volume: 0.2 μL; and temperature increase conditions: 80° C. (3min), 80 to 150° C. (10° C./min), 150 to 250° C. (5° C./min), 250° C.(20 min); and one selected from the group consisting of: a thermalcationic polymerization initiator, an acid anhydride-based curing agentand a curing accelerator, and a photo-cationic polymerization initiator.10. The curable composition according to claim 9, further comprising onekind, or two or more kinds selected from the group consisting of anepoxy compound other than the compound represented by the Formula (1),an oxetane compound and a vinyl ether.
 11. The curable compositionaccording to claim 9, wherein the thermal cationic polymerizationinitiator is selected from the group consisting of aromatic sulfoniumsalt-based thermal cationic polymerization initiators, aromatic iodoniumsalt-based thermal cationic polymerization initiators and aluminumcomplex-based thermal cationic polymerization initiators.
 12. Thecurable composition according to claim 11, wherein the thermal cationicpolymerization initiator is an aromatic sulfonium salt-based thermalcationic polymerization initiator.
 13. The curable composition accordingto claim 10, wherein, in cases where the curable composition does notcomprise any of the epoxy compound other than the compound representedby the Formula (1), the oxetane compound and the vinyl ether, thecontent of the thermal cationic polymerization initiator is from 0.1 to15 parts by mass with respect to 100 parts by mass of the compositioncontained in the curable composition; and in cases where the curablecomposition comprises one kind, or two or more kinds selected from thegroup consisting of the epoxy compound other than the compoundrepresented by the Formula (1), the oxetane compound and the vinylether, the content of the thermal cationic polymerization initiator isfrom 0.1 to 15 parts by mass with respect to 100 parts by mass of thetotal amount of the epoxy composition, the epoxy compound other than thecompound represented by the Formula (1), the oxetane compound and thevinyl ether, which are contained in the curable composition.
 14. Thecurable composition according to claim 10, wherein, in cases where thecurable composition does not comprise the epoxy compound other than thecompound represented by the Formula (1), the content of the acidanhydride-based curing agent is from 0.6 to 1.2 equivalents with respectto one epoxy equivalent of the composition contained in the curablecomposition; and in cases where the curable composition comprises theepoxy compound other than the compound represented by the Formula (1),the content of the acid anhydride-based curing agent is from 0.6 to 1.2equivalents with respect to one epoxy equivalent of a mixture of epoxycompounds composed of the composition and the epoxy compound other thanthe compound represented by the Formula (1), which are contained in thecurable composition.
 15. The curable composition according to claim 10,wherein, in cases where the curable composition does not comprise theepoxy compound other than the compound represented by the Formula (1),the content of the curing accelerator is from 0.1 to 10 parts by masswith respect to 100 parts by mass of the composition contained in thecurable composition; and in cases where the curable compositioncomprises the epoxy compound other than the compound represented by theFormula (1), the content of the curing accelerator is from 0.1 to 10parts by mass with respect to 100 parts by mass of the total amount ofthe composition and the epoxy compound other than the compoundrepresented by the Formula (1), which are contained in the curablecomposition.
 16. The curable composition according to claim 9, whereinthe curing accelerator is an imidazole-based curing accelerator.
 17. Thecurable composition according to claim 11, wherein the content of thecomposition is from 10 to 99% by mass.
 18. The curable compositionaccording to claim 9, wherein the photo-cationic polymerizationinitiator is an aromatic sulfonium salt-based photo-cationicpolymerization initiator.
 19. The curable composition according to claim10, wherein, in cases where the curable composition does not compriseany of the epoxy compound other than the compound represented by theFormula (1), the oxetane compound and the vinyl ether, the content ofthe photo-cationic polymerization initiator is from 0.1 to 20 parts bymass with respect to 100 parts by mass of the composition contained inthe curable composition; and in cases where the curable compositioncomprises one kind, or two or more kinds selected from the groupconsisting of the epoxy compound other than the compound represented bythe Formula (1), the oxetane compound and the vinyl ether, the contentof the photo-cationic polymerization initiator is from 0.1 to 20 partsby mass with respect to 100 parts by mass of the total amount of thecomposition, the epoxy compound other than the compound represented bythe Formula (1), the oxetane compound and the vinyl ether, which arecontained in the curable composition.
 20. The curable compositionaccording to claim 18, wherein the content of the composition is from 1to 50% by mass.
 21. The curable composition according to claim 10,wherein the epoxy compound other than the compound represented by theFormula (1) is selected from the group consisting of glycidyl ether-typeepoxides, glycidyl ester-type epoxides and alicyclic epoxides.
 22. Amethod of producing a cured product, the method comprising the step ofcuring the curable composition according claim
 9. 23. A cured productfrom the curable composition according to claim 9.